Cephaelin propyl ether.



.15 product, especially in the form of a salt.

UNITED STATES mam orrrcu.

JOHN W. MEADER, F INDIANAPOLIS, INDIANA, ASSIGN OR TO THE ELI LILLY AND COMPANY, OF INDIANAPQLIS, INDIANA, A CORPORATION OF INDIANA.

1,219,573; No Drawing.

To all whom it may concern:

' Be it known that I, JOHN W. MEADER, a

citizen of the United States, residing at Indianapolis, Marion county, and State of Indiana, have invented and discovered certam new and useful Improvements in "jgepliaelin Propyl Ether, of which the folwlng is a specification. The 'nvention relates to the previously unknown ephaelin propyl ether, to which may be givenfthe formula G, I-I ,O N OC H,,

in"whichfthe hydrogen of the' hydroxyl group of cephaelin has been replaced by a propyl group.

his compound is a valuable medicinal Its uses are similar .to those of emetin and s it may be administered in larger doses than propyl ether 1 by suitable methods.

thatcompound owing to its less toxicity.

. The compound may be prepared by treating cephaelin with an alkali metal and a propyl haloid and isolating the cephaelin process in detail may be carried out as follows: I 46.6 grams of cephaelin and 4.6 grams 0 sodium are dissolved in about 4.00 cubic cen- .now exists in solution is isolated by recov ering the alcohol, dissolving in dilute hydrochloric .acid,.-making ammoniacal and extracting with ether. The ether solution of cephaelin propyl ether and unchanged cephaelin is extracted with an excess of dilute caustic soda solution toremove the cephaelin and evaporated'to dryness on a water bath. The compound maybe further Specification of Letters Patent.

The

CEPHAELIN PROPYL ETHER.

purified by dissolving in an acid, crystallizing as a salt, dissolving in water, making ammoniacal, extracting with ether, recovering the ether and drying in vacuum.

In the above process potassium may be substituted for sodium and propyl iodid for propyl bromid. The absolute alcohol may be replaced by any other suitable solvent, for instance amyl alcohol.

Cephaelin propyl ether is a varnish like substance easily soluble in alcohol, ether, and chloroform. It dissolves in acids to form salts. The hydrobromid crystallizes in concentric groups of white'needles. The hydrochlorid and nitrate are also crystal- What I claim is:

1. The propyl ether of cephaelin.

Patented Mar. 26, 1917. Application filed July 17,19 15. Serial No. 40,485.

2. A propyl compound of cephaelin con- I cephaelin an alkali metal, a propyl haloid and a solvent] 4:. The process of producing cephaelin propyl ether by treating cephaelin with sodium ethylate and propyl bromid.

5. The process of producing a propyl ether of cephaelin which comprises treating cephaelin with an alkali metal alcoholate v and a propyl haloid.

In Witness whereof, I have hereunto set my hand and seal at Indianapolis, Indiana, this 15th day of July, A. D. nineteen hun dred and fifteen.

. J OHN' WV. ME-ADER. [L.s.] Witnesses:

E. W. BRADFORD,

A. G. R1011. I 

